diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index cea68ebd0..e2eaea053 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -31,10 +31,13 @@ jobs:
         if: ${{ matrix.python-version == 3.8 && steps.pip-cache.outputs.cache-hit != 'true' }}
         run: |
           sudo apt-get install libxslt-dev libxml2-dev -y
+      - name: Update pip
+        if: ${{ steps.pip-cache.outputs.cache-hit != 'true' && matrix.python-version != '2.7' }}
+        run: |
+          python -m pip install --upgrade pip
       - name: Install project dependencies
         if: ${{ steps.pip-cache.outputs.cache-hit != 'true' }}
         run: |
-          python -m pip install --upgrade pip
           pip install -r requirements-dev.txt
 
   lint:
@@ -60,10 +63,14 @@ jobs:
       with:
         path: ${{ steps.pip-cache.outputs.dir }}
         key: pip-${{ matrix.python-version }}-${{ hashFiles('**/setup.py') }}
+    # Update PIP - recent version does not support PY2 though
+    - name: Update pip
+      if: ${{ matrix.python-version != '2.7' }}
+      run: |
+        python -m pip install --upgrade pip
     # Still need to properly install the dependencies - it will only skip the download part
     - name: Install project dependencies
       run: |
-        python -m pip install --upgrade pip
         pip install -r requirements-dev.txt
     - name: Lint with flake8
       run:
@@ -99,9 +106,12 @@ jobs:
       if: ${{ matrix.python-version == 3.8 }}
       run: |
         sudo apt-get install libxslt-dev libxml2-dev -y
-    - name: Install project dependencies
+    - name: Update pip
+      if: ${{ matrix.python-version != '2.7' }}
       run: |
         python -m pip install --upgrade pip
+    - name: Install project dependencies
+      run: |
         pip install -r requirements-dev.txt
         pip install pytest-cov
     - name: Test with pytest
@@ -148,9 +158,12 @@ jobs:
       if: ${{ matrix.python-version == 3.8 }}
       run: |
         sudo apt-get install libxslt-dev libxml2-dev -y
-    - name: Install project dependencies
+    - name: Update pip
+      if: ${{ matrix.python-version != '2.7' }}
       run: |
         python -m pip install --upgrade pip
+    - name: Install project dependencies
+      run: |
         pip install -r requirements-dev.txt
     - name: Test ServerMode/Coverage
       env: